Head Over Heels (2001)
Four supermodel roommates. One regular girl. The guy next door doesn't stand a chance.
Freddie Prinze Jr. week is in full effect over here at Stale Popcorn. Before tomorrow’s issue, which is a GRAND SLAM HOME RUN HIT IT OUT OF THE PARK BASES LOADED trashclassic (hope that didn’t give it away), we need to first pause and take a moment to reflect on one movie released during Freddie’s 1999-2001 hot streak that I never knew existed until this week. Turns out, that’s for a good reason. This movie breaks Freddie out of his usual territory of heartthrob college or high school student and places him alongside Monica Potter for a wild caper involving murder coverup, eastern European crime syndicates, fashion models and really bad toilet humor. You have no idea what movie I’m talking about, do you? Well, that’s okay, this one seems to have snuck out into the world and despite earning just a few hundred thousand dollars short of returning its budget, this one was no success and seems to have slipped away into obscurity. What movie am I referring to? The 2001 bomb Head Over Heels, of course, where Monica Potter plays an art restorer who is failing at love until she moves into an apartment full of supermodels and falls for the cool fashion industry guy across the street (Freddie), yet nothing is as it seems! This was a weird one but nonetheless, it’s from Freddie’s golden era and I had no idea it existed, so we’re gonna crack into it.
Head Over Heels is one of the first features from director Mark Waters who would eventually gift us with the superior 2003 Freaky Friday remake and Mean Girls. It’s funny to see how much better Mr. Waters gets with his next features, because this one was kind of a dud. That doesn’t mean I didn’t enjoy it, of course! You guys know me. Critics hated it though. It currently sits right alongside the rest of Freddie’s streak from this year at a whopping 10% on Rotten Tomatoes. I won’t keep you in suspense any longer. Let’s get into it.
We meet Amanda (Potter) who regales us with her backstory. She’s from Iowa but moved to New York City and she deems herself to have the worst judgement in men. Just like any pretty, white, blonde movie protagonist, she insists she chooses the WORST partners, despite the fact that there are people out there actually stuck in dangerous partnerships and hers just involved dishonest men. We hear about her junior high and high school boyfriends. Amanda has a pretty cool job restoring renaissance paintings for the Met Museum. Her friend Lisa (China Chow) brings her a coffee from Seattle’s Best. Remember when they were still around before Starbucks just decided “brand synergy” and converted them all to Starbucks? I feel like I saw an empty one in Connecticut recently. Lisa is telling Amanda about a “new hottie” she’s trying to get with and tells Amanda she should try for a department transfer so she doesn’t end up becoming an old spinster like the other women in the renaissance restoration department. She is assigned to restore a messed up The Bacchanal and quips that she enjoys art more than real life because in the paintings, the subjects can stay happy and in love forever. That’s a lovely sentiment. She tells Lisa she is going to surprise her boyfriend with dinner and the old spinsters tell her she’s going to die alone because she’s too distracted by her job to find true love. They love spelling this stuff out. I think one of the spinsters is sleeping with the old man who is their boss. This is weird.
Upon entering her boyfriend Michael’s (Timothy Olyphant) apartment, she finds him in the middle of sex with a lingerie model. Michael doesn’t really care that he’s caught and just says it’s not what it looks like. Amanda remarks that this is in their bed, so this must be both of their apartment. Damn. That’s double painful. Lisa consoles her but mentions that it’s strange Amanda will go weak in the knees in love about a painting but can never do that for a man. Chill, Lisa, paintings are beautiful. Monica vows to focus on work so she can forget about Michael and Lisa spoons her and they sleep.
The next day, Lisa is on the hunt for a new apartment. In a new building, a dog runs up to Amanda leaving her scared, but no worries! The dog’s owner Jim (Prinze) comes up to apologize and Amanda seems to have the “love at first sight” look on her face. Either that or a concussion. She tells Jim to learn to control his dog, but he says it’s his neighbor’s dog who he walks as the neighbor had a hip replacement. The dog tries to jump on Amanda and knocks her into Jim. Amanda tries to say it was nice to meet his “huge dog” but accidentally says “huge dong” like six times then just says “huge dick” so she’s clearly flustered and the dog, not Jim’s suave confidence during her nervousness, seems to calm her. The dog like attacks some other people so Jim has to go.
Amanda views the apartment and let me tell you something; this place is dynamite. One of those “there is no way this is in NYC for $500 per person” places. Amanda’s room will be tiny but she has a walk-in closet the size of a downtown Zara. Turns out this is going to be a fun fish out of water comedy because Holly (Tomiko Fraser), who is showing Amanda the apartment, is amazed that Amanda works. You see, Holly and her roommates Roxana (Ivana Miličević), Candi (Sarah O’Hare), and Jade (Shalom Harlow) are all supermodels, and not just supermodels, but the last four remaining “non-smoking supermodels in Manhattan,” so this should be a fun contrast. We know how much I love fish out of water comedies! The model agency pays for these women to live in this swanky apartment and they rent out the room Amanda will be in. This makes more sense, kind of. They think she doesn’t like models but she mentions that she was recently cheated on by her ex with a model so it’s a soft spot but they vow to get along.
Amanda moves her stuff in and is surrounded by all the models who are topless and want to borrow Amanda’s shirt. There is a group of suited men standing outside the apartment waiting for attention from the models or something. This becomes a reoccurring thing where rich guys line up outside the apartment hoping for a date. They make fun of these men for not having real Gucci ties and shit and we see a nice contrast as the models are superficial and Amanda isn’t. They want her to go out and join them, as they never have to pay to live the good life, but she insists she stay in and tells the models about her restoration job. She speaks with Candi about how beauty can be found in flaws when Candi says she can’t go out in public because she’s recovering from a surgery to fix her uneven ears or something. At this point, Amanda spots Jim in the apartment across from her window. Candi tells Amanda all about Jim and how he’s some kind of fashion consultant. I am not absorbing these details that well, I’m sorry.
The next day, the giant dong dog tackles Amanda again and her and Jim flirt to swelling music. Amanda reveals she knows Jim’s name but he doesn’t remember telling her his name and seems suspicious. Amanda is nervous and says she has the runs instead of “I have to run” and Jim is charmed by her nervousness. At dinner with the three models who aren’t recovering from ear surgery, they try and get Amanda to go out with Jim but she just muses that they’d end up falling in love and he’d cheat on her. The models explain their system to Amanda, showing her that they eat their fancy dinners in the spotlight while a bunch of thirsty ass guys watch from the sidelines waiting to pay for things for them. I need that life for real. Thirsty ass guys, please pay me to eat at Michelin starred restaurants while I wear designer clothing. Please?
Amanda and Candi spy on Jim. Amanda makes a bunch of weird suspicions about Jim, most disturbingly that Girl Scouts he buys cookies from are child prostitutes. Okay? Aaaaaanyway, all of the models think he’s hot. Amanda worries he’s gay because he’s too perfect, which was also a weirdly overused trope from the time period, but one of the models insists he’s straight because he wears boxers and has no framed pictures of his mother?? Well, as a boxer-brief wearing straight man who has at least one picture of his mother framed, I’m glad these stereotypes have been reclaimed for everyone. I just love my mom! Jade takes like spy-level pictures and tell Amanda to go talk to Jim at the fashion industry party he seems to be having. Candi keeps getting cosmetic procedures because she gets a discount. Amanda discusses how Jim has a “renaissance structure” to his face. How perfect. The models give Amanda a model-style makeover to make her more appealing to Jim to a club version of “Take a Chance on Me” because, once again, it’s the year 2001. Amanda says she looks like “a skank” in their selection, and their selection looks actually pretty conservative for being called skank clothes, but I digress. Amanda doesn’t seem too fun. Maybe Jim should meet Jade?
The models coach Amanda on keeping her butt cheeks clenched and keeping her nipples hard to attract Jim. Jim is just pretty cringy with how he acts around the models and agents and Amanda looks apprehensive. She tells Jade she was wrong about Jim and goes to leave. She finds Jim on the fire escape and she tells him she was the models’ science experiment. He tells Amanda how he wishes he could leave the party with her, as he is forced to kiss peoples’ asses and act like someone he’s not for his job. Oh, what a relief for Amanda! It was all for work. She says he’s like two different people and he agrees that she could consider it that. Jim wants Amanda to stay and they sit and talk. The models see this from the window and approve.
Amanda and Jim end up getting deep in their conversations. Jim says he keeps getting disappointed thinking everyone is a good person and finding out he’s wrong, which Amanda considers her problem. There is clearly some chemistry between these two because Freddie Prinze Jr. can be charming with any actress even if there’s no actual screen chemistry. Jim has to go be nice to a Belgian designer and Amanda leaves but Jim chases after her to ask her out. They kiss, aww! They make a plan for a date on Saturday and Amanda collapses from going weak in the knees.
Back at the apartment, Amanda tells the models of her success and they celebrate. They spy on Jim once again and see him with a woman. Uh oh, suspicious! Jim closes the blinds which raises the suspicions of the models. Amanda accepts this because sadly she’s used to being lied to and there being another woman. She watches the silhouettes of Jim and the other woman and HOLY SHIT JIM JUST KILLED HER WITH LIKE A BAT OR SOMETHING! We clearly see Jim’s shadow strike the woman’s shadow. The blinds are then lifted and Jim peers out. Amanda calls the police to report a murder.
The cops come and take Amanda’s story and seemingly also enter Jim’s apartment. The models are idiotically making the police report complicated by just mentioning all the things they imagined from spying on Jim and the cop tells Amanda he doesn’t believe any of them although he has to still investigate the accusation. The cop keeps insulting Amanda’s intelligence thinking she’s also a model. Like it takes a fucking genius to become a cop LMAO. Anyway, the models arrive back from a trip to Atlanta and conclude Jim must be innocent because he is still in the apartment paying a cleaning staff. Amanda goes back to the police and the same cop blows Amanda off saying Jim is a nice guy and the woman just fell and he helped her out.
Amanda is working on restoring the painting at work and it looks like she’s placing Jim’s head in the painting? Weird. The models come into Amanda’s job to tell her she was projecting her fears onto Jim and to still go out with him as it seems there’s no evidence he killed anyone. Amanda is defensive but the old spinsters she works with insist she go for it, lest she end up like them. Amanda tries to say she knows something is wrong with Jim but everyone shrugs her off and wants her to go out with him. Amanda vows to prove he’s a bad guy.
Amanda and Roxana try to seduce the building super to get Jim’s apartment key. The women are out of breath from hiking upstairs, as they apparently broke the elevator. They enter Jim’s apartment to spy and try and find evidence that he killed the woman. They find a dress shirt with a bloodstain that turns out to be ketchup. They find a box of chef knives and use them to slice cheese. Uh oh, Jim is coming home! The models and Amanda are gonna get caught! Holly, back at the apartment, throws a kiwi at Jim’s window to alert them about Jim and they hide in his shower, except Amanda who hides under his desk. Jim makes a phone call discussing a meeting that was a success. We have CLASSIC comic tension as Jim almost discovers the women but it turns out Jim has to use the bathroom while the models are in the shower. He should call a doctor; it sounds like he was fighting for his life in there. The models do a great job keeping quiet despite being disgusted. I have no idea why they put this scene in the film but hey.
Back at work, Amanda is discussing how there’s still something not right about Jim to Lisa. Just then, Jim shows up to surprise Amanda with flowers and is impressed that Amanda is restoring a Titian painting. He tries to get her to run off for a drink now before their date but she’s skittish and says she needs to work. He kisses her cheek and leaves. Lisa snaps her out of it and tells her to keep spying, and we still have half the movie to go.
We get a NYC scenery montage as the ladies spy on Jim with “hilarious” antics interspersed. The men that Jim meets with see the ladies follow him and remark that they need to check Amanda out to make sure they don’t have “another Megan O’Brien” on their hands. Megan is the name of the woman Amanda thinks that Jim murdered. Interesting! Back at Jim’s building, Amanda bribes the super with a pretty dress for access to Jim’s storage space. Jim of course is right behind her when she goes to try and check it out because this is a movie so she runs and hides. She sees Jim carry a large, heavy duffel out and assumes it’s a body. She calls the models to inform them and let them know she’s following Jim in Central Park as she thinks he’s trying to bury the body. This should go well.
Turns out Jim is pulling out baseball equipment as lights go on and he’s on a baseball diamond and kids come out of nowhere. Oh wow, he was a Little League coach the whole time. Amanda vows to stop investigating Jim, at least long enough to have her date. One of the guys Jim was speaking to previously, Halloran (Jay Brazeau), has come to try and get an eye on Amanda under the guise of her restoring an old Russian painting with possible bullet holes in the bottom. Halloran notes the view the women have of Jim working out. The next day, Holly has her first big runway show and Jim is there. Someone asks Jim about Megan O’Brien, as no one has seen her since Jim’s party. Holly overhears.
Amanda and Jim are on their date and the models are spying on them, making sure Amanda is safe. I don’t know how the models are hiding/blending in at this weird dive bar, but hey. Jim gets a page and tells Amanda to meet him outside. The models hide in the men’s room right before some plumbers come in to repair a toilet in the bathroom. Their dialogue is suggestively sexual and the models can only hear what they’re saying so you know where this goes. Jim returns the page and whoever he talks to on the phone knows he’s out with Amanda. He says “if they want a body, I’ll give em a body” before hanging up. The models get blasted with a bunch of shit because for some reason, this movie doesn’t know if it wants to be a thriller, a romcom or a juvenile toilet movie.
Jim takes Amanda to like an aquarium or something and shows her manatees. They kiss and he takes her home. Jim asks if they’re moving too fast as Amanda hardly knows him. There’s some kind of knockoff Goo Goo Dolls band’s song playing while they discuss love at first sight and how Jim wanted to kiss her the moment they met. Back at the apartment, the models are cleaning the shit off themselves and spying on Amanda and Jim who they see getting intimate. They want to tell Amanda about Jim but they don’t want to ruin everything. Post-coital, Jim vows to start a religion to worship Amanda’s body so I guess we can say the sex went well. Amanda wants Jim to tell her everything about him and he shows her his knife throwing skills to the horror of the models who are watching. Jim’s knife throwing is pretty impressive as he managed to spear a fly without even trying.
Upon arriving home, the models are impressed with Amanda’s sexual prowess. Amanda happily tells them Jim is taking her to Shelter Island for the weekend with something big to tell her. The models minus Holly are excited but Holly is suspicious that Jim is taking her away. Holly tells Amanda she heard Jim mention Megan O’Brien but Amanda tells Holly not to worry as she leaves for work with Lisa. Things seem to be going well for Amanda until she passes a newsstand and sees a tabloid cover stating that Megan O’Brien’s body was found with no clothes, horrifying Amanda.
In an elevator, Halloran tells Jim he likes the way Jim does business and is proud of how Jim handled the “problem with the woman” to which Jim asks about how money from Antwerp gets back to him. Halloran wants to expand Jim’s role in whatever their organization is. As they exit the elevator, Amanda approaches Jim and Halloran with the tabloid, pressing him on what happened to Megan since it was stated that she tripped. Amanda confesses she saw Jim kill Megan and that she had been spying on Jim. Amanda asks how Jim knows Halloran and Halloran pulls a gun on Jim saying they should all have a talk as Halloran’s men guard the entrance. Just then, Jim pulls out his knives. He slashes Halloran and uses his throwing skills to incapacitate Halloran’s men. He grabs Amanda and stuffs her on the floor of his car as he drives away, keeping her safe from gunfire. Halloran tells his men that the women have seen too much and they take off.
Jim confesses that Halloran is actually Vadiim Strukov, a connected Russian criminal. He tells Amanda he’s undercover with the FBI and so is Megan and that the “murder” of Megan was staged because Strukov was watching from the rooftop and Jim staged Megan’s murder to prove his loyalty after Megan’s cover was blown. He says the picture in the tabloid was planted as the criminals were suspicious no body surfaced. He explains that the criminals use fashion execs to launder money through dresses from Antwerp. I wonder if they ever use any Dries or Demeulemeester? Anyway, Jim says Amanda blew his cover before he was able to find out how these guys actually make their money. Jim apologizes to Amanda as he didn’t plan to get involved with her and makes a call. Amanda sees the bullet holes in Jim’s car and realizes they’re the same size as in the Russian painting she had been restoring for Halloran/Strukov. They deduce the models are in danger and race back to the apartment, but Halloran’s men are already there with guns drawn. Jim pulls a gun on the henchmen while they escape with the girls and the big ass dog from the beginning causes a distraction to Jim giving the henchmen the upper hand. Amanda and Jim catch the models up on what’s going on while they are all captive at a garment factory. Jim confesses his actual name is Bob Smoot, which is a cooler name. One of the models mentions how all that comes from Antwerp are diamonds, which, um, have you never heard of the Antwerp Six? It’s called fashion, sweaty, look it up. They realize that the Russians are smuggling diamonds out of Russia illegally by studding the dresses with them. One of the henchmen, Harold (Raoul Ganeev), notes that Strukov never let him take a dress for his girlfriend which now makes sense. Even the henchmen were in the dark! This is a real criminal organization!
Jim tries to get Harold to turn state’s evidence for him and promises Harold access to Hawaii via the witness protection program. Roxana is able to flirt with Harold in Russian long enough to distract him so Jim can punch him in the balls and take the keys to free them all. Bob/Jim realizes the diamonds are replaced with CZ’s before the dresses go back out and Amanda is too hung up on the fact that everything between them has been a lie. HOLY SHIT AMANDA THIS IS NOT THE TIME! Harold comes to and chase music plays as Bob and the models escape and dive into a limo with fashion designer Alfredo (Stanley DeSantis) to make their escape. Alfredo muses about how all his models cancelled on him for his five o’clock runway show and while he states that he’s stressed about it, he’s just like in a limo drinking champagne so it doesn’t seem like he really cares. Regardless, the models are willing to fill in for the show and Bob makes a call saying he can bust Strukov at Alfredo’s show.
Bob tries to give direction but Amanda is being so god damned insufferable. This is life and death, lady! Worry about your relationship later! Amanda is dragged into the dressing room with the models and Strukov is on the phone with henchmen directing them to remove Bob and Amanda. They give chase through the dressing room where Bob comes back to help Amanda and fight off the henchmen. Amanda walks out onto the runway and falls on her face. She strolls the catwalk looking like she’s trying to sneak downstairs for a midnight snack without waking anyone. Clearly, she lacks to model gait. Strukov sees her front row but backstage Bob is wrecking the henchmen, just absolutely walloping them. One of the henchmen attempts to walk the catwalk to get Amanda but the models knock him over. During the distraction and all the photography, Amanda ends up on Strukov’s shoulders. Bob tells her to trust him as he punches Strukov out. Alfredo’s show is praised as Avant Garde. The FBI gives the models and Amanda special accommodations for assisting in this crackdown.
Bob pulls Amanda aside and apologizes for the way things went and asks if they can start over. Amanda says she is unsure if she’s ready to start a new relationship. Bob is whisked off by one of the agents to complete paperwork. Later Amanda restores the renaissance painting and the face looks like Bob’s. She gives a voiceover that she regrets screwing up and letting the one person she had a connection with get away as Bob moved away and had his lines of contact cut after completing this mission. Lisa and Candi seem to be dating and Lisa says Amanda shouldn’t give up on Bob. Amanda goes running off to find him at the aquarium. She thinks she sees him but its some other generic guy. On the street, Bob approaches Amanda in plain clothes saying he just moved into the neighborhood and they introduce themselves as their actual selves. Bob claims he got promoted to a boring desk job with the FBI and shows Amanda his new apartment where now he has a view overlooking the models’ apartment. Mirroring Amanda’s going weak in the knees earlier, Bob goes weak in the knees and they kiss. He closes the blinds and that’s our movie.
So yeah, this was a hot mess. Monica Potter is great but I don’t think her input is matched by any of the other characters. We could have transferred her character to a more serious movie and had her role work out. Likewise, if we stuck an actress who acted a little goofier in this, we could have had the perfect formula. Honestly Freddie is pretty good in this too but it’s just all so goofy. Needless to say, I’m glad Mark Waters got his act together and hit us over the head with some straight blassics eventually. Head Over Heels, though? I don’t know about this one. I for one will definitely be rewatching it, but I really don’t know how much I can recommend it to you kind readers. But it is currently streaming on Starz and it’s only like 80 minutes so you can find out for yourself. Don’t say I didn’t warn ya.